Incredibly fond memories of time spent with my sister in high school. She taught me more than I taught her.
Beth my sister and I have always been very close while we were growing up. We took baths together and we've always walked around the house in our underwear until significant changes started to become obvious. My sister was developing very nicely and I was becoming more endowed and some mornings would wake up with a hard on which is quite noticeable when you are just walking around in your underwear. But there were times when we would catch glimpses of each other in the morning while getting ready for school considering we shared the same bathroom and I was usually the one waiting for her.
We both started dating when we hit high school and sometime around the middle of the year in ninth grade Beth came home from school and said she wanted to talk with me about something. We went into her room and she closed the door and had me sit on her bed.
She wanted to know if I had been having any kind of sexual encounters with my girlfriend because her boyfriend wanted her to give him a hand job over the weekend and she said she wasn't quite ready for that yet. She wanted to know if Tiffany had done anything like that with me.
I told Beth that we kissed a lot and touched each other through our clothes but that we hadn't gotten any further yet. That's when Beth asked me if I would be willing to show her how a hand job was done.
'Mom actually showed me kind of how on a dildo but it's not the real thing and I really want to get this right before I try it on Rick,' she said.
'Mom is really cool about sex but she can only show me so much, please! I will be indebted to you forever,' Beth exclaimed.
'So what else has Mom taught you about sex?' I asked.
'She taught me how to masturbate and she has a lot of really cool toys that she lets me play with. I've been masturbating for about a year now.'
'I know you probably feel a little weird about this but we have seen each other a little in the past and as awkward as this feels right now, I'm ready for this.' she said.
And with that Beth took off all her clothes until she was totally naked.
'If this doesn't get you totally hard, nothing will.'
I was totally in awe of her nakedness. For the first time I was seeing my sister in all her beauty and she was gorgeous. Not only that but her pussy was totally shaven except for a very small patch of hair just above it and her nipples were rock hard.
'Alright, time to show me what you got.'
Beth actually came over and undid my belt and pulled my pants down and I stepped out of them. My hard on was raging as evident from the bulge in my underwear and she pulled those down and my cock was like inches from her face.
'You have a gorgeous cock, perfect size too. This is going to be so much fun getting to play with this' and she grabbed it and without me showing her anything and just started stroking it.
'I thought you wanted me show you how, but I'm getting the feeling that you've been practising with that dildo and just want a live cock to practice with,' I said.
'This feels so much better than Mom's dildo. Just let me know if I'm doing it right or if I need to slow down or speed up. That's the part I'm more unsure of,' Beth exclaimed.
'Lets just put it this way sis, if you want to prolong the session, you need to slowly play with it and stroke it slower or I'm going to cum on you in no time,' I aid.
With that Beth slowed her pace down not wanting to end so soon. She spit on it a couple of times to give it some lubrication and along with my precum was more than sufficient lubrication.
'Can we move to the bed so I can play with you a little while your doing me', I asked.
'Sure, but let me get something from Mom's room first. I have something that I want to try out with you.' Beth left and came back with a pink rubber looking dildo and some lube.
'You are going to love this toy. It'll be just perfect and I guarantee you your orgasm will be incredibly enhanced by this.'
'What is it?'
'It is called an anal plug and you insert it in your ass with some lube and it gives you the feeling of a cock filling your ass. I know your not gay but I use it a lot and so I thought you might want to give it a go. Trust me on this, OK?' If you don't like it, I'll stop. Besides, I want it in my ass when I cum so I've got it whether you like it or not.'
'I'm game for anything that brings you pleasure. I'll give it a shot.'
We climbed up on the bed and Beth had me lay back as she took a little of the lube and rubbed it around my anus. Actually it felt really good and she inserted her finger after a few seconds and with her other hand started stroking my cock again.
'So what do you think so far with just my finger?' she asked.
'It feels great. I'm willing to go for it,' I said.
Beth rubbed some lube on the plug and slowly inserted it until the thicker part was in past the opening and bottomed out.
'That's it. It's in and now I can devote my attention to this gorgeous cock of yours.'
The pressure of the plug wasn't as bad as I expected and Beth was really into giving my cock her fullest attention. I started playing with her nipples which she told me she loved.
She had me gently squeeze them and it didn't take long for them to get nice and hard.
'Just so you know, when I get ready to cum I like my nipples squeezed really hard. So when I tell you I'm cumming, you need to pinch them really hard. I usually use clothes pins'
Beth continued her stroking of my cock and with all the talk and the plug in my ass I was ready to unload.
'Sis I am just about ready to blow my load. So stroke hard and fast and get ready to see your first load of cum.'
Beth was ready and with my encouragement she started pumping as hard and as fast as her hand would let her.
'I'm cumming, don't stop stroking once I start shooting. I need you to keep stroking it until everything comes out, OK?
'OK,'she said. And with that I started spurting several loads of cum all over her hand and my stomach.
'That was awesome. I love the feel of it. A little sticky with a musky kind of smell.
This will make great lube for my ass. She pulled the plug out of my butt and rubbed it in the cum that was on my stomach and then inserted it into her ass.
'THIS is by far my favorite toy of Mom's toy box. I'm not sure if I'll ever do it for real because this is small compared to the real thing. OK time for you to play with my sweet spot.'
And with that Beth pulled her pussy lips apart and placed her finger on the spot she wanted me to rub.
'This is my clit. As it gets enlarged from you playing with it, It's kind of like you getting hard. It'll become sensitive and after rubbing it will bring me to orgasm after a few minutes. So have at it.'
And so I started rubbing it with a couple fingers as she laid back and got into what I was doing. I pulled on her nipple with my other hand and she played with her other one.
She really got into moaning and pushing up against my hand and within probably three minutes was ready.
'I'm almost there, same thing as you, rub harder and faster, and don't stop until I tell you.'
I was stroking her clit with intensity and speed and in 30 seconds she was screaming.
'Don't stop, almost there,' and with that she let loose. 'Ah fuck, yes, yes, yes!
Her body finally relaxed and she grabbed my hand and had me stop but not before she brought it up to her mouth and licked my fingers clean.
'That's the other thing I love, the taste of my pussy after I've cum.'
I rubbed her pussy which was as wet as could be and tasted her scent. I have to admit, it was pleasant.
'You are an amazing brother and I just want to thank you for allowing me the pleasure of practising my technique on you and for getting me off.'
Beth became very proficient in all aspects of pleasuring of the cock and I in return learned a whole new aspect to the art masturbation of the female persuasion.
'Sis, Thank you for teaching me more than I could have ever taught you!' 'I Love You!'